@David Thompson has had considerable success getting started in this area.  

The 2 biggest considerations we see investors face (in my narrowly defined bubble) are #'s 3 & 4 that Dave listed above

If it will not rent for that, and I don't see some very strong evidence for other considerations - significant property value appreciation, redevelopment, commercial rezoning, etc - then I pass.

The buyer (any of the 3 mentioned) will need to put up option consideration to have the right (but not the obligation) to buy.  

If you are renting it because you have very good reason to believe it will rise in value, that could work.

While I'm still not 100% sure we have made the right move in terms of numbers, I'm pretty confident we are in the right track based on what we have taken into consideration Vs what we've been reading.Now back to my question, our first rental is been on the market for a little over 2 weeks and after reducing the price a little we got a better response from potential renters.

While I'm still not 100% sure we have made the right move in terms of numbers, I'm pretty confident we are in the right track based on what we have taken into consideration Vs what we've been reading.Now back to my question, our first rental is been on the market for a little over 2 weeks and after reducing the price a little we got a better response from potential renters.

How should I structure the deal with him so I don't get burnt and anything else I need to take into consideration ?

sold thanks everyone for the consideration, I'll keep posting deals I find!

Screen applicants as normal and select the most qualified without consideration for the contractors offer.